Über die Spaltung von Tetrahydrofuran mit Methansulfobromid

Sieber, Gerhard

doi:10.1002/jlac.19606310122

Cited by 20 publications

(9 citation statements)

References 14 publications

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“…Freshly distilled styrene (1.9 g, 18 mmol) and MeSO 2 Br [11], (2.86 g, 18 mmol) in anhydrous CH 2 Cl 2 (15 ml) were placed in a quartz test tube. The reaction mixture was irradiated with UV light for 10 h at 20ºC.…”

Section: Methodsmentioning

confidence: 99%

Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates

Васин

Bolusheva

Razin

2008

Chem Heterocycl Comp

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It is known [1, 2] that bromomethyl vinyl sulfones and, in particular, the sulfone 1a undergo a Michael induced Ramberg-Bäcklund (MIRB) addition reaction when treated with sodium alcoholate to give alkyl allyl ethers. Benzyl α-bromovinyl sulfone reacts with different nucleophiles by a similar scheme to give allyl derivatives [3]. As members of the series of α-bromovinyl bromomethyl and β-bromovinyl bromomethyl sulfones the dibromosulfones 2a and 3a also react via an MIRB reaction with sodium methylate, presumably through a bromomethyl ethynyl sulfone stage to form a vinyl phenyl ketone dimethyl ketal in both cases [2]. It is also known that some α-bromovinyl sulfones unable to take part in the Ramberg-Bäcklund reaction cyclize to sulfonyl-substituted aziridine derivatives when treated with primary amines in DMSO [4]. Similarly, several α-chlorovinyl sulfones not able to undergo the Ramberg-Bäcklund reaction undergo Michael induced addition cyclization to give sulfonyl-substituted dihydrofuran and cyclopropane derivatives when treated with ethylacetoacetate or diethyl malonate enolates [5].The examples given point to a variety of reactions of halo-substituted methyl vinyl sulfones in Michael induced addition reactions and open up a short route to the formation of acyclic, cyclic, and heterocyclic structures difficult to prepare by other methods.In this work we have studied the reactions of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates with a view to determining the effect of the position and number of bromine atoms on the _______ Dedicated to Professor A. A. Potekhin's memory. __________________________________________________________________________________________ 1 N. P. Ogarev

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Section: Methodsmentioning

confidence: 99%

Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates

Васин

Bolusheva

Razin

2008

Chem Heterocycl Comp

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“…Elution with 3:2 hexane-acetone gave three fractions. The first fraction (3.5 mg) was pure methyl 4,6-0-benzylidene-3-0-methyl-/3-D-glucopyranoside (9) identical with an authentic sample (mixture melting point and ir spectra). The second fraction (18 mg) was a mixture of 8 and 9 (monitored by tic using 95:5 benzene-2-propanol as eluent), whereas the third fraction (82 mg) was pure methyl 4,6-O-benzylidene-3-0-methyl-/3-o-mannopyranoside (8).…”

Section: Methodsmentioning

confidence: 76%

“…The reduction of 2 was effected with sodium borohydride in methanol. The reason for using sodium borohydride for reduction of 2 rather than lithium aluminum hydride was based on the observation that sodium borohydride produces more axial alcohol than lithium aluminum hydride in reductions of alicyclic ketones, indicating a greater effective size of the borohydride species.7 The crude reduction product, as expected, consisted almost exclusively of methyl 4,6-O-benzylidene-3-0-methyl-/3-D-mannopyranoside (8) [the ratio of D-manno (8) to D-gluco derivative (9) was 19:1],…”

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confidence: 89%

Steric and electrostatic interactions in reactions of carbohydrates. II. Stereochemistry of addition reactions to the carbonyl group of glycopyranosiduloses. Synthesis of methyl 4,6-O-benzylidene-3-O-methyl .beta.-D-mannopyranoside

Miljković¹,

Gligorijevic²,

Miljković³

1974

J. Org. Chem.

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“…Another improvement is the use of methanesulfonyl bromide16 for conversion of benzylic alcohols to bromides. In the synthesis of dendrimers with aryl benzyl ether linkages, the most popular methods are bromination with CBr 4 /PPh 3 followed by Williamson ether synthesis,17 and the direct reaction of benzylic alcohol with phenols by the Mitsunobu reaction 18.…”

Section: Resultsmentioning

confidence: 99%

Photo‐ and Redox‐Active Dendritic Molecules with Soft, Layered Nanostructures

Kikuzawa

Nagata

Tahara

et al. 2006

Chemistry An Asian Journal

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Molecules with one photoactive group (porphyrin) and multiple redox-active groups (ferrocenes) are described. The molecules are based on dendritic frameworks, with the ferrocenyl groups attached at the "internal" positions and the porphyrin attached at the focal point, leading to a characteristic layer architecture. Molecules of up to the third generation were synthesized and examined. The results of 1H NMR spectroscopy and fluorescence quenching indicated that the ferrocenyl groups at the second layer approach the core porphyrin most closely, which is consistent with the results of molecular-dynamics simulations. The electrochemistry of the molecules was also examined in detail, and a new formula is proposed for the analysis of multiple-electron transfer in these "redox-pool" molecules.

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Über die Spaltung von Tetrahydrofuran mit Methansulfobromid

Cited by 20 publications

References 14 publications

Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates

Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates

Steric and electrostatic interactions in reactions of carbohydrates. II. Stereochemistry of addition reactions to the carbonyl group of glycopyranosiduloses. Synthesis of methyl 4,6-O-benzylidene-3-O-methyl .beta.-D-mannopyranoside

Photo‐ and Redox‐Active Dendritic Molecules with Soft, Layered Nanostructures

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